4-Ethenyl-7-hydroxy-8-methyl-9,10-dihydrophenanthrene-1-carboxylic acid

Details

• Internal ID: 80b0af6d-d26f-4d0d-94f2-63544bd2dcf8
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Hydrophenanthrenes
• IUPAC Name: 4-ethenyl-7-hydroxy-8-methyl-9,10-dihydrophenanthrene-1-carboxylic acid
• SMILES (Canonical): CC1=C(C=CC2=C1CCC3=C(C=CC(=C32)C=C)C(=O)O)O
• SMILES (Isomeric): CC1=C(C=CC2=C1CCC3=C(C=CC(=C32)C=C)C(=O)O)O
• InChI: InChI=1S/C18H16O3/c1-3-11-4-5-15(18(20)21)14-7-6-12-10(2)16(19)9-8-13(12)17(11)14/h3-5,8-9,19H,1,6-7H2,2H3,(H,20,21)
• InChI Key: ANNWAJFLVFSWGC-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₃
• Molecular Weight: 280.30 g/mol
• Exact Mass: 280.109944368 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.81
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.7004	70.04%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7975	79.75%
OATP2B1 inhibitior	-	0.5677	56.77%
OATP1B1 inhibitior	+	0.8989	89.89%
OATP1B3 inhibitior	+	0.9564	95.64%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5384	53.84%
P-glycoprotein inhibitior	-	0.9264	92.64%
P-glycoprotein substrate	-	0.8832	88.32%
CYP3A4 substrate	-	0.5625	56.25%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8804	88.04%
CYP3A4 inhibition	-	0.7622	76.22%
CYP2C9 inhibition	+	0.5600	56.00%
CYP2C19 inhibition	+	0.5155	51.55%
CYP2D6 inhibition	-	0.8542	85.42%
CYP1A2 inhibition	+	0.7610	76.10%
CYP2C8 inhibition	+	0.4808	48.08%
CYP inhibitory promiscuity	-	0.5942	59.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9011	90.11%
Carcinogenicity (trinary)	Non-required	0.4913	49.13%
Eye corrosion	-	0.9882	98.82%
Eye irritation	+	0.7287	72.87%
Skin irritation	+	0.5611	56.11%
Skin corrosion	-	0.8567	85.67%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5781	57.81%
Micronuclear	-	0.6741	67.41%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.6303	63.03%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6363	63.63%
Acute Oral Toxicity (c)	III	0.5891	58.91%
Estrogen receptor binding	+	0.6448	64.48%
Androgen receptor binding	+	0.6665	66.65%
Thyroid receptor binding	+	0.5245	52.45%
Glucocorticoid receptor binding	+	0.8483	84.83%
Aromatase binding	+	0.5536	55.36%
PPAR gamma	+	0.7871	78.71%
Honey bee toxicity	-	0.9547	95.47%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.8400	84.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.71%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.95%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.53%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.70%	95.56%
CHEMBL4208	P20618	Proteasome component C5	87.18%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.01%	95.50%
CHEMBL3194	P02766	Transthyretin	86.83%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	85.12%	98.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.41%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.11%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.87%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.27%	97.36%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.94%	90.24%

Plants that contains it

• Juncus effusus
• Rubia cordifolia

Cross-Links

• PubChem: 9993796
• NPASS: NPC261247
• LOTUS: LTS0129083
• wikiData: Q104915306